Department of Chemistry , Moscow State University , Leninskie Gory 1-3 , Moscow 11999 , Russian Federation.
Org Lett. 2019 Nov 15;21(22):9080-9083. doi: 10.1021/acs.orglett.9b03471. Epub 2019 Nov 1.
Trifluorodiazoethane is a widely explored trifluoroethylating reagent, which is suitable for the preparation of a large number of fluorine-containing organic molecules. Nevertheless, CFCHN has some disadvantages, such as volatility, storage instability, toxicity, and explosiveness. We report the application of trifluoroacetaldehyde -tosylhydrazone as a CFCHN precursor capable of generating in situ trifluorodiazoethane under mild basic conditions. Copper-catalyzed P-H, O-H, S-H, and C-H insertion reactions of trifluoroacetaldehyde -tosylhydrazone revealed its wide applicability in the synthesis of trifluoroethyl-containing substances.
三氟重氮乙烷是一种广泛探索的三氟乙基化试剂，适用于制备大量含氟有机分子。然而，CFCHN 也存在一些缺点，如挥发性、储存稳定性差、毒性和爆炸性。我们报告了三氟乙醛-对甲苯磺酰腙作为 CFCHN 前体的应用，它能够在温和的碱性条件下原位生成三氟重氮乙烷。三氟乙醛-对甲苯磺酰腙的铜催化 P-H、O-H、S-H 和 C-H 插入反应揭示了其在合成含三氟乙基物质中的广泛适用性。
